System Hacking: gaining access

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Questions and Answers

Which of the following best describes the primary goal of system hacking?

  • To gain unauthorized access to a target system. (correct)
  • To disrupt network services for a short period.
  • To identify and report system vulnerabilities to the vendor.
  • To encrypt sensitive data on a system for ransom.

Which of the following Windows components stores user passwords in a hashed format?

  • The Security Account Manager (SAM) database (correct)
  • The Active Directory schema
  • The Group Policy Objects (GPO)
  • The Windows Registry

Which authentication protocol is used by default in modern Windows systems for stronger client/server authentication?

  • NTLM
  • challenge-response
  • Kerberos (correct)
  • LAN Manager (LM)

What is the primary function of the SYSKEY function in relation to the SAM file in Windows NT 4.0 and later?

<p>To partially encrypt the password hashes within the SAM file. (C)</p>
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What is the main characteristic of a 'non-electronic' password attack?

<p>It relies on social interaction or observation to obtain passwords. (B)</p>
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What type of password attack does the tool pwdump7 facilitate?

<p>Extracting password hashes from a SAM database. (A)</p>
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Which of the following password attacks involves an attacker intercepting and relaying NTLM authentication requests between a client and a server?

<p>NTLM Relay Attack (D)</p>
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In the context of Kerberos authentication, what component serves as a trusted third party to verify user identities?

<p>Key Distribution Center (KDC) (B)</p>
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What is the main characteristic of Rainbow Table Attacks?

<p>They use pre-computed hashes to recover passwords. (C)</p>
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What is the primary method by which attackers exploit the 'Do not require Kerberos preauthentication' setting in an Active Directory environment?

<p>By extracting and cracking the ticket granting ticket (TGT). (B)</p>
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Which of the following attacks involves attempting a single commonly used password across multiple user accounts before moving to the next password?

<p>Password spraying attack (B)</p>
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Which type of attack involves the attacker obtaining some information about the password, such as knowing the password contains a two-digit number?

<p>Rule-based attack (A)</p>
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What is the purpose of a 'mask attack' in password cracking?

<p>To narrow down the list of possible passwords by using a pattern. (A)</p>
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In an NTLM authentication process, what is the purpose of the 'nonce' sent by the domain controller to the client computer?

<p>To provide a random string that the client must encrypt with the user password hash. (A)</p>
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What underlying aspect of human behavior does social engineering exploit to gain unauthorized access?

<p>Trusting nature of people (B)</p>
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Which of the following tools can be used to perform password attacks such as brute-force attacks, dictionary attacks, and mask attacks?

<p>Hashcat (A)</p>
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How do attackers exploit Single-Sign-On (SSO) in Windows environments during a hash injection/Pass-the-Hash (PtH) attack?

<p>Inject a compromised LAN Manager (LM) or NTLM hash into a local session. (B)</p>
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What is the primary objective of attackers employing LLMNR/NBT-NS poisoning techniques within a network?

<p>To collect NTLMv2 hashes for cracking or relaying. (D)</p>
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What is the primary purpose of 'dumpster diving' as a system hacking technique?

<p>To collect sensitive information from discarded materials. (B)</p>
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During a password change operation in newer Windows versions, what value does the SAM file store for LM hashes if LM hashes are disabled?

<p>A 'dummy' value. (B)</p>
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In the context of system security, what does the term 'shoulder surfing' refer to?

<p>Observing someone entering their password. (D)</p>
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Why are dictionary attacks generally more effective than brute-force attacks?

<p>Dictionary attacks use a list of words commonly used as passwords. (D)</p>
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What is the primary goal of using Trojans/Spyware/Keyloggers in system hacking?

<p>To capture user credentials and sensitive information. (A)</p>
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Which of the following is a type of password attacks that does not lead to any changes in the system but passively monitor or record the data passing over the communication channel?

<p>Passive Online Attacks (B)</p>
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What are the two main elements of Windows OS used to perform name resolution for hosts present on the same link?

<p>LLMNR and NBT-NS (D)</p>
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During which phase of system hacking is password cracking typically employed?

<p>Gaining access (C)</p>
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What is a common mitigation against password spraying attacks?

<p>Enforcing multi-factor authentication. (C)</p>
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Which type of attack is similar to brute-force attacks but recovers passwords from hashes with a more specific set of characters based on information known to the attacker?

<p>Mask attack (C)</p>
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What is the purpose of using custom charsets in hashcat?

<p>To define the type of characters for brute-forcing passwords. (C)</p>
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Why is encrypting the nonce with a user password hash in the NTLM authentication process important?

<p>To verify that the client computer knows the user's password. (D)</p>
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In the context of password guessing, which strategy would BEST improve an attacker's chances of success?

<p>Finding and targeting known default accounts. (C)</p>
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What is the primary advantage of using tools like thc-hydra for password attacks?

<p>The tool allows attackers to use different options on how to attack with logins and passwords. (B)</p>
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What is the initial step when performing dictionary attack using John the Ripper?

<p>Download wordlist rockyou.txt. (D)</p>
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Flashcards

Password Cracking

The process of recovering passwords from data transmitted or stored within a system.

Non-Electronic Attack

A password attack not needing technical skills; methods include social engineering.

Active Online Attack

When attacker communicates directly with target to gain access.

Passive Online Attack

Attack that doesn't alter system, attacker monitors.

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Offline Attack

Attacker recovers clear text passwords from hash dumps.

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Shoulder Surfing

Technique of stealing passwords by watching users enter them.

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Dumpster Diving

Key attack method using trash to find sensitive information.

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Dictionary attack

A file loaded into a cracking app that runs against user accounts.

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Brute-Force Attack

A program tries every character combination.

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Rule-Based Attack

Used when the attacker has some info about the password.

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Password Spraying Attack

Targets mult. user accounts simultaneously using one set of passwords.

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Pass the Ticket

Technique for authenticating a Kerberos user without the password.

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NTLM Relay Attack

Involves intercepting and relaying NTLM auth requests.

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Microsoft Authentication

Hashes stored in Windows SAM or Active Directory DB.

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NTLM Authentication

Default authentication using challenge/response.

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Kerberos Authentication

Network authentication via secret-key crypto.

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Security Accounts Manager (SAM)

Windows DB to manage user accounts.

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Study Notes

  • System hacking is a critical goal for attackers, involving techniques like footprinting, scanning, enumeration, and vulnerability analysis.
  • The focus will be on tools and techniques attackers use to compromise systems.
  • The key objectives are to explain access techniques, apply privilege escalation, maintain remote access, understand rootkits, use steganography, hide evidence, and implement countermeasures.

Gaining Access

  • The CEH hacking methodology (CHM) includes attacker steps that will be discussed.
  • The primary step involves attackers using various techniques to gain access to the target system.
  • These techniques involve cracking passwords, exploiting buffer overflows, and exploiting identified vulnerabilities.

Microsoft Authentication: How Hash Passwords Are Stored in Windows SAM?

  • Windows stores user passwords in the Security Account Manager (SAM) or Active Directory database, always hashed, never as clear text.
  • Tools such as pwdump7, Mimikatz, DSInternals, Hashcat, and PyCrack are used to extract the password hashes.
  • pwdump7 extracts LM and NTLM password hashes from the SAM database.

Microsoft Authentication: NTLM Authentication Process

  • NTLM has two authentication protocol types: NTLM authentication and LM authentication protocol.
  • These protocols store the user's password in the SAM database using different hashing methods which will be discussed.
  • Windows runs the password through a hash algorithm for authentication.
  • The steps in the NTLM process include the client sending a login request, the DC sending a challenge, the client encrypting it and sending it back, and the DC comparing.

Microsoft Authentication: Kerberos Authentication

  • Microsoft upgraded its default authentication protocol to Kerberos, which offers stronger security than NTLM.
  • Steps include the user requesting authentication from the AS, the AS granting a ticket, the client requesting service from the TGS, and access being granted to the application server.

Cracking Passwords: Microsoft Authentication

  • Steps are performed for user authentication using three mechanisms provided by Microsoft.
  • Windows uses the Security Accounts Manager (SAM) database or Active Directory Database to manage user accounts and passwords in hashed format.
  • The system does not store passwords in plaintext format but in a hashed format, to protect them from attacks.
  • The SAM database is implemented as a registry file, and the Windows kernel obtains and keeps an exclusive filesystem lock on it for security.
  • Attackers can dump the on-disk contents of the SAM file using various techniques to make password hashes available for offline brute-force attacks.
  • The SAM file uses an SYSKEY function (in Windows NT 4.0 and later versions) to partially encrypt the password hashes.

NTLM Authentication

  • NT LAN Manager (NTLM) is a default authentication scheme.
  • It performs authentication using a challenge/response strategy and does not rely on any official protocol specification.
  • NTLM has two protocols: NTLM authentication protocol and LAN Manager (LM) authentication protocol.
  • These protocols use different hash methodologies to store user’s passwords in the SAM database.

Kerberos Authentication

  • Kerberos is a network authentication protocol that provides strong authentication for client/server applications through secret-key cryptography.
  • Kerberos is a network authentication protocol that provides strong authentication for client/server applications through secret-key cryptography.
  • The messages are protected against replay attacks and eavesdropping.
  • The Key Distribution Center (KDC) contains an authentication server (AS) and a ticket-granting server (TGS).

How Hash Passwords Are Stored in Windows SAM?

  • Windows stores user passwords in the SAM database file, located at %SystemRoot%\system32\config\SAM.
  • Windows mounts the SAM file in the registry under HKEY_LOCAL_MACHINE\SAM.
  • The system stores LM or NTLM hashed passwords.
  • NTLM superseded LM hash, but new versions of Windows still support LM hashes for backward compatability.
  • Tools like pwdump7 extract password hashes from the SAM database.
  • pwdump7 extracts LM and NTLM password hashes of local user accounts from the SAM database.

NTLM Authentication Process

  • NTLM involves challenge-response authentication (LM, NTLMv1, NTLMv2) with varying encryption levels.
  • The client and server negotiate the authentication protocol using the Microsoft-negotiated Security Support Provider (SSP).
  • Microsoft recommends Kerberos as its default authentication protocol because of its stronger authentication for cleint/server applicaitons.

Password Cracking

  • Password cracking is recovering passwords from stored or transmitted data in a computer system.
  • It can help users recover lost passwords and system administrators check for vulnerabilities.
  • Attackers also use password cracking to gain unauthorized system access.
  • Password-cracking techniques are often successful due to typically weak of guessable passwords.

Types of Password Attacks

  • Non-Electronic Attacks: The attacker requires no technical knowledge.
  • Active Online Attacks: The attacker directly communicates with the victim’s machine.
  • Passive Online Attacks: The attacker does not interacts with the authorizing party when cracking passwords.
  • Offline Attacks: The attacker copies the password file and cracks passwords on own system.

Non-Electronic Attacks

  • Social engineering, shoulder surfing, and dumpster diving are the three types of non-electronic attacks.
  • Social engineering exploits human behavior to gain information.
  • Employees may sometimes not value the information they possess.
  • The best defense is to educate, train, and create awareness about this attack and the value of information.

Shoulder Surfing

  • Shoulder surfing is a technique that steals passwords by watching users enter them.
  • The attacker looks at the keyboard or screen as the user logs in.
  • This attack can occur in checkout lines at stores when users enter PINs.

Dumpster Diving

  • Dumpster diving involves searching through trash to find sensitive information.
  • Attackers can find documents, discarded media with password files, manuals, reports, and credit card numbers.
  • The information gathered can be used to perform other attacks, such as social engineering.

Active Online Attacks: Dictionary, Brute-Force, and Rule-based Attack

  • A dictionary file is loaded into the cracking application that runs against user accounts in dictionary attacks.
  • The program tries every combination of characters until the password is broken in brute-force attacks.
  • The attacker gets some information about the password in rule-based attacks.

Acrive Online Attacks: Peform Dictionary and Brute-Force Attack

  • The rockyou.txt wordlist should be found in the /usr/share/wordlist directory, but can also be downloaded from GitHub.
  • Run command to generate a customized password.
  • The following John the Ripper command should be run to start cracking NTLM hashes.

Active Online Attacks: Hash Injection/Pass-the-Hash (PtH) Attack

  • The Pth attack injects a compromised hash into a local session and validates network resources.
  • The extracted hash is used by attackers to log on to the domain controller.

Active Online Attacks: LLMNR/NBT-NS Poisoning

  • LLMNR and NBT-NS are Windows OS elements used for host name resolution on the same link.
  • The attacker cracks the NTLMv2 hash obtained from the victim’s authentication process.
  • The extracted credentials are used to log on to the host system in the network.

AS-REP Roasting (Cracking TGT)

  • The attackers target users that have the "Do not require Kerberos preauthentication" option enabled.
  • Attackers extract ticket granting ticket (TGT) and cracks it to obtain user passwords, with the obtained user passwords.
  • The attack allows the attackers to gain illegal access, move laterally within the network, and escalate privileges.

Password Spraying Attack

  • This involves targeting multiple user accounts with a common password set, exploiting account lockout policies.
  • It can be performed through ports like MSSQL (1433/TCP), SSH (22/TCP), FTP (21/TCP), SMB (445/TCP), Telnet (23/TCP).
  • The command-line tool thc-hydra is useful for hackers use for password spraying attacks.

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